(R)-4-methyl-1-nonanol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-4-methyl-1-nonanol
• 英文别名: (4R)-4-methylnonan-1-ol
• 化学式: C₁₀H₂₂O
• 分子量: 158.284
• InChiKey: HECVGHIJHFNAIL-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-4-methyl-1-nonanol 生成 (R)-4-甲基壬酸
  参考文献：
  名称：

  TANAKA, YUICHI;HONDA, HIROSHI;OHSAWA, KANJU;YAMAMOTO, IZURU, NIXON NOYAKU GAKKAJSI, 14,(1989) N, S. 197-202

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-(R)-methyl-5-hydroxypentanoate 在 lithium aluminium tetrahydride 、 magnesium 、 lithium bromide 作用下， 以 吡啶 、 乙醚 、 丙酮 为溶剂， 反应 20.5h， 生成 (R)-4-methyl-1-nonanol
  参考文献：
  名称：

  Carpita, Adriano; Magistris, Elisabetta De; Rossi, Renzo, Gazzetta Chimica Italiana, 1989, vol. 119, # 2, p. 99 - 106

  摘要：

  DOI：

文献信息

• α-Chloro-β,γ-ethylenic Esters: Enantiocontrolled Synthesis and Substitutions
  作者：Douglas T. Genna、Christopher P. Hencken、Maxime A. Siegler、Gary H. Posner

  DOI：10.1021/ol102142a

  日期：2010.10.15

  γ-seleno-α,β-ethylenic esters, when treated with sulfuryl chloride and ethyl vinyl ether in hexanes, produced α-chloro-β,γ-ethylenic esters in 65−75% yields, with ee values of 95−97%, and with 1,3-syn transfer of chirality. Reaction of these allylic chloride electrophiles with methylcuprate and with sodium azide nucleophiles afforded exclusively γ-substituted-α,β-ethylenic esters with faithful anti-transfer

  手性非外消旋的γ-硒代-α，β-烯键式酯，在己烷中用硫酰氯和乙基乙烯基醚处理后，以65-75％的产率产生α-氯-β，γ-烯键式酯，ee值为95-97 ％，并具有1，3-syn手性转移。这些烯丙基氯亲电试剂与甲基铜酸酯和叠氮化钠亲核试剂反应，仅得到γ-取代的-α，β-烯键式酯，在毫克数级上具有可靠的手性抗转移性。
• Stereoselective Synthesis of Sex Pheromone (R)-4-Methyl-1-Nonanol: Non-Cross-Linked Polystyrene Supported Oxazolidinone as a Chiral Auxiliary
  作者：Cuifen Lu、Donglai Li、Qiuyan Wang、Guichun Yang、Zuxing Chen

  DOI：10.1002/ejoc.200800758

  日期：2009.3

  (R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworm (Tenebrio Molitor L.), was synthesized by using non-cross-linked polystyrene supported oxazolidinone as a chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addition of an organocopper reagent to non-cross-linked polystyrene supported N-crotonoyoxazolidinone, and the target product was obtained in an overall

  (R)-4-Methyl-1-nonanol 是黄粉虫 (Tenebrio Molitor L.) 的性信息素，是通过使用非交联聚苯乙烯负载的恶唑烷酮作为手性助剂合成的。立体选择性合成是通过将有机铜试剂不对称迈克尔加成到非交联聚苯乙烯负载的 N-巴豆酰恶唑烷酮中来实现的，并且在七个步骤中以 41.8% 的总收率获得了目标产物，对映体过量为 98%。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Stereoselective synthesis of the sex pheromone of the yellow mealworm using (S)-4-benzyloxazolidinone as chiral auxiliary
  作者：D. L. Li、C. F. Lu、G. C. Yang、Z. X. Chen

  DOI：10.1007/s10600-010-9636-z

  日期：2010.7

  (R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworn (Tenebrio molitor L.), was synthesized with high stereoselectivity using (S)-4-benzyloxazolidinone as chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addition of organocopper reagent to N-crotoyloxazolidinone, and the target product was obtained in an overall yield of 41.8% over 7 steps.

  (R)-4-Methyl-1-nonanol 是黄粉蚧 (Tenebrio molitor L.) 的性信息素，使用 (S)-4-benzyloxazolidinone 作为手性助剂以高立体选择性合成。通过有机铜试剂与N-巴豆酰恶唑烷酮的不对称迈克尔加成实现立体选择性合成，7步得到目标产物，总收率为41.8%。
• SN2′ Alkylation of Chiral Allylic CyanohydrinO-Phosphates with Organocuprates
  作者：Alejandro Baeza、Carmen Nájera、José M. Sansano

  DOI：10.1002/ejoc.200600822

  日期：2007.3

  This work has been supported by the DGES of the Spanish Ministerio de Educacion y Ciencia (MEC) (CTQ2004-00808/BQU), the Generalitat Valenciana (CTIOIB/2002/320, GRUPOS03/134 and GV05/144) and the University of Alicante.

  这项工作得到了西班牙教育部长和 Ciencia (MEC) (CTQ2004-00808/BQU)、Generalitat Valenciana (CTIOIB/2002/320、GRUPOS03/134 和 GV05/144) 和阿利坎特大学的 DGES 的支持.
• Optically pure acyclic bifunctional compounds from (?)-menthone. Synthesis ofR-4-methyl-1-nonanol, the sex pheromone of the larger flour beetle (Tenebrio molitor L.)
  作者：V. N. Odinokov、G. Yu. Ishmuratov、M. P. Yakovleva、R. L. Safiullin、V. D. Komissarov、G. A. Tolstikov

  DOI：10.1007/bf00702016

  日期：1993.7

  novel methyl-branched chirones were prepared starting from (−)-menthone and making use of a novel, efficient, and selective oxidant, decanepersulfonic acid (DPSA). Optically pure (4R)-methyl-1-nonanol, the sex pheromone of the larger flour beetle (Tenebrio molitor L.), was synthesized.

  以 (-)-薄荷酮为原料，利用新型、高效和选择性的氧化剂癸烷过磺酸 (DPSA)，制备了许多新型甲基支化手性酮。合成了光学纯 (4R)-甲基-1-壬醇，即较大的面粉甲虫 (Tenebrio molitor L.) 的性信息素。